1-Phenyl-1,2-propanedione → 2-Methyl-6,7-dinitro-3-phenylquinoxaline

HRID 584674Notes

Reaction equation

HRID 584674 reaction equation
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([NH2:13])=[C:6]([NH2:14])[CH:5]=1)([O-:3])=[O:2].[C:15]1([C:21](=O)[C:22](=O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH3:23][C:22]1[C:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:14][C:6]2[C:7](=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:13]=1

Participants

4

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 44419034,5-Dinitrobenzene-1,2-diamine

Product 1

HCID 223411162-Methyl-6,7-dinitro-3-phenylquinoxalineYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Dinitro-1,2-phenylenediamine (890 mg, 4.5 mmol) (G. W. H. Cheeseman, J. Org. Soc. 1170-5, 1962) was mixed with 1-phenyl-1,2-propanedione (800 mg, 5.4 mmol) in ethanol (18 ml). The mixture was heated to reflux for 4 hours. The ethanol was removed by evaporation and the remaining brown oil was suspended in dichloromethane (20 ml). Purification by column chromatography on silica gel eluting with dichloromethane followed by recrystallisation from ethanol yielded the title compound (200 mg, 14%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe ethanol was removed by evaporation
  4. customPurification by column chromatography on silica gel eluting with dichloromethane
  5. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-facd989c39224d68bf4dce36c8df2915
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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